The BEST episodes of Billy on the Street season 5

Every episode of Billy on the Street season 5, ranked from best to worst by thousands of votes from fans of the show. The best episodes of Billy on the Street season 5!

Billy Eichner takes to the streets to test the knowledge of unsuspecting pedestrians. Billy asks questions with his patented fast-paced and goofy style, covering topics from Lil' Wayne to Meryl Streep, for a fun time that is part game show and part comedy.

Last Updated: 11/24/2024Network: truTVStatus: Ended
Do Gay People Care About John Oliver? with John Oliver!
star
8.22
36 votes

#1 - Do Gay People Care About John Oliver? with John Oliver!

Season 5 - Episode 7 - Aired 1/3/2017

This week, Billy and John Oliver take to the streets to find out if gay people care about him!

Watch Now:Amazon
Immigrant or Real American? with Jon Hamm!
star
8.02
58 votes

#2 - Immigrant or Real American? with Jon Hamm!

Season 5 - Episode 1 - Aired 11/15/2016

In the season 5 premiere, Billy and Jon Hamm take to the streets to find out if anyone will have a threesome with them! Later, Billy plays "Immigrant or Real American?" with Kevin the bisexual office manager. Plus, Billy plays the first For A Dollar, Quizzed in the Face and Lightning Round games of the new season!

Watch Now:Amazon
Curbside Conga Line with James Corden
star
8.00
32 votes

#3 - Curbside Conga Line with James Corden

Season 5 - Episode 8 - Aired 1/10/2017

Billy takes the show on the road to LA with special guest James Corden! James joins Billy as he desperately tries to appeal to the masses with a Carpool Karaoke-inspired game called Curbside Conga Line. Later, Robin Lord Taylor and Billy take on a new obstacle course called "Can You Separate the Art from the Artist?".

Watch Now:Amazon
Miracle on 34th Streep with Andy Samberg!
star
7.97
34 votes

#4 - Miracle on 34th Streep with Andy Samberg!

Season 5 - Episode 4 - Aired 12/6/2016

Billy and Andy Samberg play the brand new game Was At My Wedding or Possibly Killed Tupac?; Billy and Andy introduce New Yorkers to some brand new superheroes; Billy is joined by Kevin the busboy to play Fox News Anchor or Pilgrim?

Watch Now:Amazon
Super Sloppy Semi-Automatic Double Dare! with Keegan-Michael Key
star
7.91
22 votes

#5 - Super Sloppy Semi-Automatic Double Dare! with Keegan-Michael Key

Season 5 - Episode 9 - Aired 1/17/2017

Billy is joined by Key and Peele star Keegan-Michael Key for the game Name 10 Gay People! Later, Billy is joined by aspiring actor Cameron to play Walking Dead or Talking Dead?

Watch Now:Amazon
Billy's Holiday Wonderland with Jacob Tremblay!
star
7.86
28 votes

#6 - Billy's Holiday Wonderland with Jacob Tremblay!

Season 5 - Episode 6 - Aired 12/20/2016

In this week's episode, Billy is joined for the first time by a child actor - the star of Room, Jacob Tremblay! Together, Jacob and Billy take to the street for a brand new Lightning Round.

Watch Now:Amazon
Lupita Nyong'o: Bring the Pain
star
7.76
38 votes

#7 - Lupita Nyong'o: Bring the Pain

Season 5 - Episode 3 - Aired 11/29/2016

This week Billy is joined by Oscar winner Lupita Nyong'o for the brand new game Gay or Old? Later, everyone's favorite contestant Elena is back with a very patriotic Lightning Round! Finally, Lupita gets to work on her first half hour comedy special in a segment called Lupita Nyong'o: Bring the Pain. Other games include Barack Obama or Jennifer Lawrence? and Rizolli or Isles?

Watch Now:Amazon
Death Rogen with Special Guest Seth Rogen!
star
7.74
43 votes

#8 - Death Rogen with Special Guest Seth Rogen!

Season 5 - Episode 2 - Aired 11/22/2016

In this week's jam-packed episode Billy hits the streets with Seth Rogen for a new segment called Death Rogen. Later, just in time for Thanksgiving, Billy and Sarah play What Does Michelle Rodriguez Bring to the Table? Finally, Annabelle the marketing intern competes in the very first Billy on the Street relay race! Other games include a new For A Dollar and Seth Vogue'n.

Watch Now:Amazon
The NY Bubble with Stephen Colbert!
star
7.59
27 votes

#9 - The NY Bubble with Stephen Colbert!

Season 5 - Episode 10 - Aired 1/24/2017

In the season finale of Billy on the Street, Billy is joined by Emmy-winner Stephen Colbert to play La La Land or Nicki Minaj? Later, everyone's favorite contestant Elena is back to answer your Twitter questions!

Watch Now:Amazon
Aziz on the Street!
star
7.58
36 votes

#10 - Aziz on the Street!

Season 5 - Episode 5 - Aired 12/13/2016

This week Billy is joined by Aziz Ansari to play the brand new game Is This a Kanye West Quote or Not? Later, Rachel Dratch is back for an exhilarating obstacle course, Escape Margot Robbie's Moment!

Watch Now:Amazon